Organoelectroluminescent compound and organoelectroluminescent device employing the same

ABSTRACT

A cyclopentaphenanthrene-based compound is easy to prepare and excellent in solubility, color purity, and color stability. The cyclopentaphenanthrene-based compound is useful as a material for forming an organic layer, in particular, an emitting layer, in an organoelectroluminescent device, and as an organic dye or an electronic material such as a nonlinear optical material.

CROSS-REFERENCE TO RELATED PATENT APPLICATION AND CLAIM OF PRIORITY

This application claims priority from Korean Patent Application No.10-2006-0096124, filed on Sep. 29, 2006, in the Korean IntellectualProperty Office, the disclosure of which is incorporated herein in itsentirety by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a cyclopentaphenanthrene-based compoundand an organoelectroluminescent device employing the same. Moreparticularly, the present invention relates to acyclopentaphenanthrene-based compound and an organoelectroluminescentdevice including an organic layer formed of thecyclopentaphenanthrene-based compound.

2. Description of the Related Art

Organoelectroluminescent devices are active emission display devicesthat emit light by recombination of electrons and holes in a thin layer(hereinafter, referred to as “organic layer”) formed of a fluorescent orphosphorescent organic compound when a current is supplied to theorganic layer. The organoelectroluminescent devices have advantages suchas lightness, simple constitutional elements, an easy fabricationprocess, superior image quality, and a wide viewing angle. In addition,the organoelectroluminescent devices can perfectly create dynamicimages, achieve high color purity, and have electrical propertiessuitable for portable electronic equipment due to low power consumptionand low driving voltage.

Eastman Kodak Co. has developed an organoelectroluminescent device witha multi-layered structure including an aluminum quinolinol complex layerand a triphenylamine derivative layer (U.S. Pat. No. 4,885,211), and anorganoelectroluminescent device including an organic light-emittinglayer formed of a low molecular weight material capable of emittinglight in a broad wavelength range from UV to infrared light (U.S. Pat.No. 5,151,629).

Light-emitting devices are self-emitting devices and have advantagessuch as a wide viewing angle, good contrast, and a rapid response time.Light-emitting devices can be classified into inorganic light-emittingdevices using an emitting layer formed of an inorganic compound andorganic light-emitting devices (OLEDs) using an emitting layer formed ofan organic compound. OLEDs show better brightness, driving voltage, andresponse speed characteristics and can create polychromatic light,compared to inorganic light-emitting devices, and thus, extensiveresearch into OLEDs has been conducted.

Generally, OLEDs have a stacked structure including an anode, an organiclight-emitting layer, and a cathode. OLEDs may also have variousstructures such as anode/hole injection layer/hole transportlayer/emitting layer/electron transport layer/electron injectionlayer/cathode or anode/hole injection layer/hole transportlayer/emitting layer/hole blocking layer/electron transportlayer/electron injection layer/cathode.

Materials used for OLEDs can be classified into vacuum-depositablematerials and solution-coatable materials according to an organic layerformation process. Vacuum-depositable materials must have a vaporpressure of 10⁻⁶ torr or more at 500° C. or less, and may be lowmolecular weight materials having a molecular weight of 1,200 or less.Solution-coatable materials must have solubility sufficient to formsolutions, and include mainly an aromatic or heterocyclic ring.

When manufacturing organoelectroluminescent devices using a vacuumdeposition process, manufacturing costs may increase due to use of avacuum system, and it may be difficult to manufacture high-resolutionpixels for natural color displays using a shadow mask. On the otherhand, when manufacturing organoelectroluminescent devices using asolution coating process, e.g., inkjet printing, screen printing, orspin coating, the manufacturing process is simple, manufacturing costsare low, and a relatively high resolution can be achieved compared towhen using a shadow mask.

However, when using solution-coatable materials, the performance (e.g.,thermal stability, color purity) of light-emitting molecules is loweredcompared to when using vacuum-depositable materials. Even though thelight-emitting molecules of the solution-coatable materials have goodperformance, there arise problems that the materials, when formed intoan organic layer, are gradually crystallized to grow into a sizecorresponding to a visible light wavelength range, and thus, the growncrystals scatter visible light, thereby causing a turbidity phenomenon,and pinholes, etc. may be formed in the organic layer, thereby causingdevice degradation.

Japanese Patent Laid-Open Publication No. 1999-003782 discloses a twonaphthyl-substituted anthracene compound that can be used in an emittinglayer or a hole injection layer. However, the anthracene compound ispoorly soluble in a solvent, and further, an organoelectroluminescentdevice using the anthracene compound has unsatisfactory characteristics.

Therefore, it still needs to develop organoelectroluminescent deviceshaving reduced driving voltage and improved brightness, efficiency, andcolor purity characteristics by virtue of blue light-emitting compoundswhich have good thermal stability and can form good organic layers.

The above information disclosed in this Background section is only forenhancement of understanding of the background of the invention andtherefore it may contain information that does not form the prior artthat is already known in this country to a person of ordinary skill inthe art.

SUMMARY OF THE INVENTION

The present invention provides a cyclopentaphenanthrene-based compoundwhich is adapted for both dry and wet processes, and has excellentthermal stability and good charge transport and emissioncharacteristics, and an organoelectroluminescent device employing thesame.

According to an aspect of the present invention, there is provided acyclopentaphenanthrene-based compound represented by Formula 1 below:

wherein each Q is independently a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup;

each Y is independently a substituted or unsubstituted C2-C30 alkylenegroup, a substituted or unsubstituted C6-C30 cycloalkylene group, asubstituted or unsubstituted C6-C30 arylene group, a substituted orunsubstituted C2-C30 heteroarylene group, or a substituted orunsubstituted C2-C30 alkenylene group;

X is hydrogen, halogen, a cyano group, a hydroxyl group, a substitutedor unsubstituted C1-C20 alkyl group, a substituted or unsubstitutedC3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxygroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C6-C30 arylalkyl group, a substituted or unsubstitutedC2-C30 heteroaryl group, —N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃,Z₄, and Z₅ are each independently hydrogen, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, asubstituted or unsubstituted C5-C20 cycloalkyl group, or a substitutedor unsubstituted C5-C30 heterocycloalkyl group;

m is an integer of 0 to 3, and when m is 2 or 3, Qs are the same ordifferent from each other;

n is an integer of 0 to 3, and when n is 2 or 3, Ys are the same ordifferent from each other;

R₁ and R₂ are each independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group, and R₁ and R₂ can be optionally linked togetherto form a substituted or unsubstituted C3-C20 aliphatic ring, asubstituted or unsubstituted C5-C30 heteroaliphatic ring, a substitutedor unsubstituted C6-C30 aromatic ring, or a substituted or unsubstitutedC2-C30 heteroaromatic ring; and;

R₃ through R₁₆ are each independently hydrogen, halogen, a cyano group,a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and

R₁₉ is hydrogen, halogen, a cyano group, a hydroxyl group, or asubstituted or unsubstituted C1-C20 alkyl group.

In one embodiment of the present invention, the

in Formula 1 may be linked together to form one of rings represented byFormulae 2 through 5 below:

wherein each R₁₇ is independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C 2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and

A is a single bond, O, S, Se, or (CH₂)_(p) where p is an integer of 1 to5.

According to an embodiment of the present invention, the compound ofFormula 1 above may be selected from compounds represented by Formulae 6through 8 below:

wherein each Y is independently a substituted or unsubstituted C2˜C30alkylene group, a substituted or unsubstituted C6˜C30 cycloalkylenegroup, a substituted or unsubstituted C6-C30 arylene group, asubstituted or unsubstituted C2-C30 heteroarylene group, or asubstituted or unsubstituted C2-C30 alkenylene group;

each Q is independently a substituted or unsubstituted C6-C30 arylenegroup or a substituted or unsubstituted C2-C30 heteroarylene group;

m is an integer of 0 to 3, and when m is 2 or 3, Qs are the same ordifferent from each other;

n is an integer of 0 to 3, and when n is 2 or 3, Ys are the same ordifferent from each other;

X is hydrogen, halogen, a cyano group, a hydroxyl group, a substitutedor unsubstituted C1-C20 alkyl group, a substituted or unsubstitutedC3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxygroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C6-C30 arylalkyl group, a substituted or unsubstitutedC2-C30 heteroaryl group, —N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃,Z₄, and Z₅ are each independently hydrogen, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, asubstituted or unsubstituted C5-C20 cycloalkyl group, or a substitutedor unsubstituted C5-C30 heterocycloalkyl group;

R₉ through R₁₆ are each independently hydrogen, halogen, a cyano group,a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group;

R₁′ and R₂′ are each independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and

each R₁₈ is independently hydrogen, halogen, a cyano group, a hydroxylgroup, a substituted or unsubstituted C1-C20 alkyl group, a substitutedor unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstitutedC5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20alkoxy group, a substituted or unsubstituted C6-C30 aryl group, asubstituted or unsubstituted C6-C30 aralkyl group, a substituted orunsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅)where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independently hydrogen, asubstituted or unsubstituted C1-C20 alkyl group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkylgroup, or a substituted or unsubstituted C5-C30 heterocycloalkyl group.

According to another aspect of the present invention, there is providedan organoelectroluminescent device including: a first electrode; asecond electrode; and at least one organic layer interposed between thefirst electrode and the second electrode, the organic layer includingthe above-described organoelectroluminescent compound.

In the embodiments of the present invention, a low molecular weightcompound obtained by reacting a cyclopentaphenanthrene compound whereinthe 2- or 6-position is functionalized with halogen, borate, aldehyde,hydroxyl, or the like, with another compound, is used as anorganoelectroluminescent material. Various substituents can beincorporated into the 4-position of the cyclopentaphenanthrene of thelow molecular weight compound, thereby enabling more stable filmformation and improving solubility in a solvent.

BRIEF DESCRIPTION OF THE DRAWINGS

A more complete appreciation of the invention, and many of the attendantadvantages thereof, will be readily apparent as the same becomes betterunderstood by reference to the following detailed description whenconsidered in conjunction with the accompanying drawings in which likereference symbols indicate the same or similar components, wherein:

FIGS. 1A through 1C are schematic views illustratingorganoelectroluminescent devices according to embodiments of the presentinvention; and

FIG. 2 is a graph illustrating emission characteristics of anorganoelectroluminescent device according to an embodiment of thepresent invention.

DETAILED DESCRIPTION OF THE INVENTION

Embodiments of the present invention will now be described more fullywith reference to the accompanying drawings, in which exemplaryembodiments of the invention are shown.

An embodiment of the present invention provides acyclopentaphenanthrene-based compound represented by Formula 1 below:

wherein each Q is independently a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup;

each Y is independently a substituted or unsubstituted C2-C30 alkylenegroup, a substituted or unsubstituted C6-C30 cycloalkylene group, asubstituted or unsubstituted C6-C30 arylene group, a substituted orunsubstituted C2-C30 heteroarylene group, or a substituted orunsubstituted C2-C30 alkenylene group;

X is hydrogen, halogen, a cyano group, a hydroxyl group, a substitutedor unsubstituted C1˜C20 alkyl group, a substituted or unsubstitutedC3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxygroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C6-C30 arylalkyl group, a substituted or unsubstitutedC2-C30 heteroaryl group, —N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃,Z₄, and Z₅ are each independently hydrogen, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, asubstituted or unsubstituted C5-C20 cycloalkyl group, or a substitutedor unsubstituted C5-C30 heterocycloalkyl group;

m is an integer of 0 to 3, and when m is an integer of 2 or 3, Qs may bethe same or different from each other;

n is an integer of 0 to 3, and when n is an integer of 2 or 3, Ys may bethe same or different from each other;

R₁ and R₂ are each independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group, and R₁ and R₂ can be optionally linked togetherto form a substituted or unsubstituted C3-C20 aliphatic ring, asubstituted or unsubstituted C5-C30 heteroaliphatic ring, a substitutedor unsubstituted C6-C30 aromatic ring, or a substituted or unsubstitutedC2-C30 heteroaromatic ring;

R₃ through R₁₆ are each independently hydrogen, halogen, a cyano group,a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and

R₁₉ is hydrogen, halogen, a cyano group, a hydroxyl group, or asubstituted or unsubstituted C1-C20 alkyl group.

In the present application, when two or more are independently selected,it means that two or more may be the same or different from each other.

According to an embodiment of the present invention, in Formula 1, m maybe an integer of 1 to 3, and n may be an integer of 1 to 3.

According to an embodiment of the present invention, in Formula 1, the

when linked together, may form rings represented by Formulae 2 through 5below:

wherein each R₁₇ is independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C 2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and

A is a single bond, O, S, Se, or (CH₂)_(p) where p is an integer of 1 to5.

The compound of Formula 1 according to the embodiment of the presentinvention may be selected from compounds represented by Formulae 6through 8 below:

wherein each Q is independently a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup;

each Y is independently a substituted or unsubstituted C2˜C30 alkylenegroup, a substituted or unsubstituted C6˜C30 cycloalkylene group, asubstituted or unsubstituted C6-C30 arylene group, a substituted orunsubstituted C2-C30 heteroarylene group, or a substituted orunsubstituted C2-C30 alkenylene group;

X is hydrogen, halogen, a cyano group, a hydroxyl group, a substitutedor unsubstituted C1-C20 alkyl group, a substituted or unsubstitutedC3-C20 cycloalkyl group, a substituted or unsubstituted C5-C30heterocycloalkyl group, a substituted or unsubstituted C1-C20 alkoxygroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C6-C30 arylalkyl group, a substituted or unsubstitutedC2-C30 heteroaryl group, —N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃,Z₄, and Z₅ are each independently hydrogen, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C2-C30 heteroaryl group, asubstituted or unsubstituted C5-C20 cycloalkyl group, or a substitutedor unsubstituted C5-C30 heterocycloalkyl group;

m is an integer of 0 to 3, and when m is 2 or 3, Qs are the same ordifferent from each other;

n is an integer of 0 to 3, and when n is 2 or 3, Ys are the same ordifferent from each other;

R₁′ and R₂′ are each independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group, and R₁′ and R₂′ can be optionally linkedtogether to form a substituted or unsubstituted C3-C20 aliphatic ring, asubstituted or unsubstituted C5-C30 heteroaliphatic ring, a substitutedor unsubstituted C6-C30 aromatic ring, or a substituted or unsubstitutedC2-C30 heteroaromatic ring;

R₉ through R₁₆ are each independently hydrogen, halogen, a cyano group,a hydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 arylalkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and

each R₁₈ is independently hydrogen, halogen, a cyano group, a hydroxylgroup, a substituted or unsubstituted C1-C20 alkyl group, a substitutedor unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstitutedC5-C30 heterocycloalkyl group, a substituted or unsubstituted C1-C20alkoxy group, a substituted or unsubstituted C6-C30 aryl group, asubstituted or unsubstituted C6-C30 aralkyl group, a substituted orunsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅)where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independently hydrogen, asubstituted or unsubstituted C1-C20 alkyl group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C2-C30heteroaryl group, a substituted or unsubstituted C5-C20 cycloalkylgroup, or a substituted or unsubstituted C5-C30 heterocycloalkyl group.

In an embodiment of the present invention, m may be an integer of 1 to3, and n may be an integer of 1 to 3.

In an embodiment of the present invention, -[Q]_(m)- may be selectedfrom the group consisting of chemical structures represented by Formulae9 through 9R below, but is not limited to:

In Formulae 6 through 8, —[Y]_(n)—X may be selected from the groupconsisting of chemical structures represented by Formulae 10A to 10R,11A to 11S, 12A to 12Q, 13A to 13LL, 14A to 14R, and 15A to 15Z below,but is not limited to:

In Formulae 9A through 15Z, R′ and R″ are each independently hydrogen,halogen, a cyano group, a hydroxyl group, a substituted or unsubstitutedC1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkylgroup, a substituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group.

In the above formulae, the “aryl group” refers to a monovalent grouphaving an aromatic ring system and may contain two or more ring systems.The two or more ring systems may be attached or fused to each other. The“heteroaryl group” refers to an aryl group in which at least one carbonatom is substituted by at least one selected from the group consistingof N, O, S, and P.

The “cycloalkyl group” refers to an alkyl group having a ring system,and the “heterocycloalkyl group” refers to a cycloalkyl group in whichat least one carbon atom is substituted by at least one selected fromthe group consisting of N, O, S, and P.

In the above formulae, the alkyl group, the alkoxy group, the arylgroup, the heteroaryl group, the cycloalkyl group, and theheterocycloalkyl group may be substituted by at least one substituentselected from the group consisting of —F; —Cl; —Br; —CN; —NO₂; —OH; aC1-C20 alkyl group which is unsubstituted or substituted by —F, —Cl,—Br, —CN, —NO₂, or —OH; a C1-C20 alkoxy group which is unsubstituted orsubstituted by —F, —Cl, —Br, —CN, —NO₂, or —OH; a C6-C30 aryl groupwhich is unsubstituted or substituted by a C1-C20 alkyl group, a C1-C20alkoxy group, —F, —Cl, —Br, —CN, —NO₂, or —OH; a C2-C30 heteroaryl groupwhich is unsubstituted or substituted by a C1-C20 alkyl group, a C1-C20alkoxy group, —F, —Cl, —Br, —CN, —NO₂, or —OH; a C5-C20 cycloalkyl groupwhich is unsubstituted or substituted by a C1-C20 alkyl group, a C1-C20alkoxy group, —F, —Cl, —Br, —CN, —NO₂, or —OH; a C5-C30 heterocycloalkylgroup which is unsubstituted or substituted by a C1-C20 alkyl group, aC1-C20 alkoxy group, —F, —Cl, —Br, —CN, —NO₂, or —OH; and a grouprepresented by —N(G₆)(G₇), where, G₆ and G₇ are each independentlyhydrogen; a C1-C10 alkyl group; or a C6-C30 aryl group which issubstituted by a C1-C10 alkyl group.

In more detail, R₁ through R₁₈ are each independently selected from thegroup consisting of a hydrogen, a halogen, a cyano group, a hydroxylgroup, a C1-C10 alkyl group, a C1-C10 alkoxy group, and a substituted orunsubstituted group as follows: a phenyl group, a biphenyl group, apentalenyl group, an indenyl group, a naphthyl group, a biphenylenyl, ananthracenyl group, an azulenyl group, a heptalenyl group, anacenaphthylenyl group, a phenalenyl group, a fluorenyl group, amethylanthryl group, a phenanthrenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, an ethyl-chrysenyl group, a picenylgroup, a perylenyl group, a chloroperylenyl group, a pentaphenyl group,a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, ahexacenyl group, a rubicenyl group, a coronenyl group, a trinaphthylenylgroup, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, anovalenyl group, a carbazolyl group, a thiophenyl group, an indolylgroup, a purinyl group, a benzimidazolyl group, a quinolinyl group, abenzothiophenyl group, a parathiazinyl group, a pyrrolyl group, apyrazolyl group, an imidazolyl group, an imidazolinyl group, an oxazolylgroup, a thiazolyl group, a triazolyl group, a tetrazolyl group, anoxadiazolyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinylgroup, a pyrazinyl group, a thianthrenyl group, a cyclopentyl group, acyclohexyl group, an oxiranyl group, a pyrrolidinyl group, apyrazolidinyl group, an imidazolidinyl group, a piperidinyl group, apiperazinyl group, a morpholinyl group, a di(C6-C30 aryl)amino group, atri(C6-C30 aryl)silyl group, and derivatives thereof.

As used herein, the term “derivative(s)” refers to the above-illustratedgroup(s) wherein at least one hydrogen is substituted by a substituentas described above.

The compound according to the embodiment of the present invention may beselected from the group consisting of compounds represented by Formulae16 through 72 below, but is not limited to:

The compound of Formula 1 according to the embodiment of the presentinvention can be synthesized using a common synthesis method. For adetailed synthesis procedure of the compound according to the embodimentof the present invention, reference will be made to the reaction schemesin the following synthesis examples.

The present invention also provides an organoelectroluminescent deviceincluding a first electrode, a second electrode, and an organic layerinterposed between the first electrode and the second electrode, theorganic layer including at least one compound represented by Formula 1above.

The compound of Formula 1 is suitable for an organic layer of anorganoelectroluminescent device, in particular an emitting layer, a holeinjection layer, or a hole transport layer.

The organoelectroluminescent device according to an embodiment of thepresent invention includes a compound which has good solubility andthermal stability and can form a stable organic layer, and thus, canshow a good driving voltage and enhanced emission characteristics (e.g.,color purity), unlike a conventional organoelectroluminescent deviceincluding a less stable organic layer when manufactured using a solutioncoating process.

The organoelectroluminescent device according to the embodiment of thepresent invention can be variously structured. That is, theorganoelectroluminescent device may further include at least one layerselected from the group consisting of a hole injection layer, a holetransport layer, a hole blocking layer, an electron blocking layer, anelectron transport layer, and an electron injection layer, between thefirst electrode and the second electrode.

In more detail, organoelectroluminescent devices according toembodiments of the present invention are illustrated in FIGS. 1A, 1B,and 1C. Referring to FIG. 1A, an organoelectroluminescent device has astacked structure of first electrode/hole injection layer/hole transportlayer/emitting layer/electron transport layer/electron injectionlayer/second electrode. Referring to FIG. 1B, anorganoelectroluminescent device has a stacked structure of firstelectrode/hole injection layer/emitting layer/electron transportlayer/electron injection layer/second electrode. Referring to FIG. 1C,an organoelectroluminescent device has a stacked structure of firstelectrode/hole injection layer/hole transport layer/emitting layer/holeblocking layer/electron transport layer/electron injection layer/secondelectrode. Here, at least one of the emitting layer, the hole injectionlayer, and the hole transport layer may include a compound according toan embodiment of the present invention.

An emitting layer of the organoelectroluminescent device according tothe embodiments of the present invention may include a red, green, blue,or white phosphorescent or fluorescent dopant. The phosphorescent dopantmay be an organometallic compound including at least one elementselected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb,and Tm.

Hereinafter, an exemplary method of manufacturing anorganoelectroluminescent device according to an embodiment of thepresent invention will be described with reference to FIG. 1C.

First, a first electrode is formed on a substrate by a deposition orsputtering process using a first electrode material with a high workfunction. The first electrode may be an anode. Here, the substrate maybe a substrate commonly used in organoelectroluminescent devices.Preferably, the substrate may be a glass or transparent plasticsubstrate which is excellent in mechanical strength, thermal stability,transparency, surface smoothness, handling property, and waterrepellency. The first electrode material may be a material withtransparency and good conductivity, e.g., indium tin oxide (ITO), indiumzinc oxide (IZO), tin oxide (SnO₂), or zinc oxide (ZnO).

Next, a hole injection layer (HIL) may be formed on the first electrodeusing various methods such as vacuum deposition, spin-coating, casting,or Langmuir-Blodgett (LB) method.

In the case of forming the hole injection layer using a vacuumdeposition process, the deposition conditions vary according to the typeof a hole injection layer material, the structure and thermalcharacteristics of the hole injection layer, etc. However, it ispreferred that the hole injection layer should be deposited to athickness of 10 Å to 5 μm at a deposition rate of 0.01 to 100 Å/sec, ata temperature of 100 to 500° C., in a vacuum level of 10⁻⁸ to 10⁻³ torr.

In the case of forming the hole injection layer using a spin-coatingprocess, the coating conditions vary according to the type of a holeinjection layer material, the structure and thermal characteristics ofthe hole injection layer, etc. However, it is preferred that thespin-coating should be performed at a coating speed of about 2,000 to5,000 rpm, and, after the spin-coating, a thermal treatment should beperformed at a temperature of about 80 to 200° C. for the purpose ofsolvent removal.

The hole injection layer material may be a compound of Formula 1 asdescribed above. In addition, the hole injection layer material may be aknown hole injection material, e.g., a phthalocyanine compound (e.g.,copper phthalocyanine) disclosed in U.S. Pat. No. 4,356,429 which isincorporated herein by reference, a Starburst-type amine derivative(e.g., TCTA, m-MTDATA, or m-MTDAPB) disclosed in Advanced Material, 6,p. 677 (1994) which is incorporated herein by reference, or a solubleconductive polymer, e.g., polyaniline/dodecylbenzenesulfonic acid(Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)(PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), orpolyaniline/poly(4-styrenesulfonate) (PANI/PSS).

The hole injection layer may be formed to a thickness of about 100 to10,000 Å, preferably 100 to 1,000 Å. If the thickness of the holeinjection layer is less than 100 Å, hole injection characteristics maybe lowered. On the other hand, if the thickness of the hole injectionlayer exceeds 10,000 Å, a driving voltage may be increased.

Next, a hole transport layer (HTL) may be formed on the hole injectionlayer using various methods such as vacuum deposition, spin-coating,casting, or LB method. In the case of forming the hole transport layerusing vacuum deposition or spin-coating, the deposition or coatingconditions vary according to the type of a used compound, but aregenerally almost the same as those for the formation of the holeinjection layer.

A hole transport layer material may be a compound of Formula 1 asdescribed above. In addition, the hole transport layer material can be aknown hole transport material, e.g., a carbazole derivative such asN-phenylcarbazole or polyvinylcarbazole; an amine derivative having anaromatic fused ring such asN,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD)or N,N′-di(naphthalene-1-yl)-N,N′-diphenylbenzidine (α-NPD), etc.

The hole transport layer may be formed to a thickness of about 50 to1,000 Å, preferably 100 to 600 Å. If the thickness of the hole transportlayer is less than 50 Å, hole transport characteristics may be lowered.On the other hand, if the thickness of the hole transport layer exceeds1,000 Å, a driving voltage may be increased.

Next, an emitting layer (EML) may be formed on the hole transport layerusing vacuum deposition, spin-coating, casting, or LB method. In thecase of forming the emitting layer using vacuum deposition orspin-coating, the deposition or coating conditions vary according to thetype of a used compound, but are generally almost the same as those forthe formation of the hole injection layer.

The emitting layer may include a compound of Formula 1 as describedabove. Here, a known fluorescent host material suitable for the compoundof Formula 1 or a known dopant material may be used together with thecompound of Formula 1. The compound of Formula 1 may be used as aphosphorescent host alone or in combination with4,4′-N,N′-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), etc.As a phosphorescent dopant, there may be used a red phosphorescentdopant (e.g., PtOEP, RD 61 (UDC)), a green phosphorescent dopant (e.g.,Ir(PPy)₃ (PPy=2-phenylpyridine)), or a blue phosphorescent dopant (e.g.,F₂Irpic).

When the compound of Formula 1 is used as a dopant, the dopingconcentration of the dopant is not particularly limited. Generally, thecontent of the dopant is 0.01 to 15 parts by weight based on 100 partsby weight of a host. When the compound of Formula 1 is used as a singlehost, the doping concentration of a dopant is not particularly limited.Generally, the content of a dopant is 0.01 to 15 parts by weight basedon 100 parts by weight of the host. When the compound of Formula 1 isused as a host in combination with another host, the content of thecompound of Formula 1 is 30-99 parts by weight based on the total weight(100 parts by weight) of the hosts.

The emitting layer may be formed to a thickness of about 100 to 1,000 Å,preferably 200 to 600 Å. If the thickness of the emitting layer is lessthan 100 Å, emission characteristics may be lowered. On the other hand,if the thickness of the emitting layer exceeds 1,000 Å, a drivingvoltage may be increased.

In a case where the emitting layer includes a phosphorescent dopant, ahole blocking layer (HBL) may be formed on the emitting layer usingvacuum deposition, spin-coating, casting, or LB method, in order toprevent the diffusion of triplet excitons or holes into an electrontransport layer. In the case of forming the hole blocking layer usingvacuum deposition or spin coating, the deposition or coating conditionsvary according to the type of a used compound, but are generally almostthe same as those for the formation of the hole injection layer. Anavailable hole blocking material may be an oxadiazole derivative, atriazole derivative, a phenanthroline derivative, BCP, an aluminumcomplex, etc.

The hole blocking layer may be formed to a thickness of about 50 to1,000 Å, preferably 100 to 300 Å. If the thickness of the hole blockinglayer is less than 50 Å, hole blocking characteristics may be lowered.On the other hand, if the thickness of the hole blocking layer exceeds1,000 Å, a driving voltage may be increased.

Next, an electron transport layer (ETL) may be formed using variousmethods such as vacuum deposition, spin-coating, or casting. In the caseof forming the electron transport layer using vacuum deposition orspin-coating, the deposition or coating conditions vary according to thetype of a used compound, but are generally almost the same as those forthe formation of the hole injection layer. An electron transport layermaterial serves to stably transport electrons from an electron donorelectrode (a cathode) and may be a known material such as anoxazole-based compound, an isoxazole-based compound, a triazole-basedcompound, an isothiazole-based compound, an oxadiazole-based compound, athiadiazole-based compound, a perylene-based compound, an aluminumcomplex (e.g.: Alq3 (tris(8-quinolinolato)-aluminum) BAlq, SAlq, orAlmq3), a gallium complex (e.g.: Gaq′2OPiv, Gaq′2OAc, 2(Gaq′2)), etc.

The electron transport layer may be formed to a thickness of about 100to 1,000 Å, preferably 200 to 500 Å. If the thickness of the electrontransport layer is less than 100 Å, electron transport characteristicsmay be lowered. On the other hand, if the thickness of the electrontransport layer exceeds 1,000 Å, a driving voltage may be increased.

An electron injection layer (EIL) may be formed on the electrontransport layer in order to facilitate the injection of electrons from acathode into the emitting layer. An electron injection layer material isnot particularly limited.

The electron injection layer material may be selected from knownmaterials such as LiF, NaCl, CsF, Li₂O, or BaO. The depositionconditions of the electron injection layer vary according to the type ofa used compound, but are generally almost the same as those for theformation of the hole injection layer.

The electron injection layer may be formed to a thickness of about 1 to100 Å, preferably 5 to 50 Å. If the thickness of the electron injectionlayer is less than 1 Å, electron injection characteristics may belowered. On the other hand, if the thickness of the electron injectionlayer exceeds 100 Å, a driving voltage may be increased.

Finally, a second electrode may be formed on the electron injectionlayer using vacuum deposition or sputtering. The second electrode may beused as a cathode. A material for forming the second electrode may bemetal or alloy with a low work function, an electroconductive compound,or a mixture thereof. For example, the second electrode material may belithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li),calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), etc.The second electrode may also be a transmissive cathode formed of ITO orIZO to provide a front-emission type device.

Hereinafter, the present invention will be described more specificallywith reference to the following working examples. However, the followingworking examples are only for illustrative purposes and are not intendedto limit the scope of the invention.

EXAMPLES

Synthesis Example 1 1) Synthesis of8,9-dihydro-4H-cyclopenta[def]phenanthrene

4H-cyclopenta[def]phenanthrene (4.75 g, 25 mmol) was put into a Parreactor bottle, and EtOH (200 ml) was added thereto. 5% Pd/C (3.99 g)was added to the reaction solution, and the resultant solution wasincubated under a hydrogen pressure of 40 psi for 24 hours. After thereaction was terminated, the reaction solution was filtered, and thefiltrate was concentrated under a reduced pressure to give a whiteproduct (4.32 g, 90%).

2) Synthesis of 2-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene

8,9-dihydro-4H-cyclopenta[def]phenanthrene (4.0 g, 20.8 mmol) was putinto a 250 ml round bottom flask (RBF), and CCl₄ (100 ml) was addedthereto. The reaction mixture was cooled to 0° C., and Br₂ (3.3 g, 20.8mmol) was dropwise added thereto. The reaction solution was incubatedfor 4 hours and a 10% NaSO₃ solution was added thereto. The organicphase was separated, concentrated under a reduced pressure, andrecrystallized from n-hexane to obtain 4.7 g of a2-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene compound.

3) Synthesis of Compound 1

2-bromo-8,9-dihydro-4H-cyclopenta[def]phenanthrene (4.45 g, 16.4 mmol)in a 250 ml round bottom flask was dissolved with xylene, ando-chloranil (4.3 g) was added thereto at room temperature. The reactionmixture was heated and refluxed in an oil bath for 72 hours. After thereaction was terminated, the reaction solution was cooled andconcentrated under a reduced pressure. The residue was purified bysilica gel column chromatography (developing solvent: n-hexane) to givea compound 1 (3.5 g, 79%).

¹H NMR (300 MHz, CDCl₃, δ): 7.98 (2H, s), 7.79 (2H, s), 7.73 (2H, s),6.94 (dd, 1H), 4.28 (2H, s)

4) Synthesis of Compound 2

2-bromo-4H-cyclopenta[def]phenanthrene (2.6 g, 9.7 mmol) and octylbromide (3.6 g, 18.5 mmol) in a 50 ml round bottom flask were dissolvedwith toluene (10 ml), and TBAB (tetrabutylammoniumbromide) (0.125 g,0.385 mmol) was added thereto. A solution of NaOH (3.1 g, 77 mmol) inwater (50 ml) was added to the reaction mixture, and the resultantsolution was refluxed for two days. After the reaction was terminated,the reaction solution was extracted with chloroform. The organic phasewas dried over MgSO₄, concentrated, and purified by silica gel columnchromatography (eluent: n-hexane). The eluate was distilled under areduced pressure to remove unreacted octyl bromide, thereby giving acompound 2 (3.6 g, 75%).

¹H NMR (300 MHz, CDCl₃, δ): 7.98 (2H, s), 7.79 (2H, s), 7.73 (2H, s),6.94 (dd, 1H), 1.93 (m, 4H), 1.21 (m, 20H), 0.87 (m, 6H), 0.65 (broad s,4H)

Synthesis Example 2 1) Synthesis of2-bromo-cyclopenta[def]phenanthren-4-one

Benzene (200 ml) was put into a 250 ml round bottom flask, and thecompound 1 (3.6 g, 13.3 mmol) was added thereto. MnO₂ (150 g) was addedto the reaction mixture, and the resultant mixture was heated andrefluxed in an oil bath for 18 hours. After the reaction was terminated,the reaction solution was filtered to remove MnO₂, and sufficientlywashed with CHCl₃, THF, and MeOH in sequence. The filtrate wasconcentrated under a reduced pressure and the residue was recrystallizedfrom acetone to give the titled compound (1.5 g, 39%).

2) Synthesis of Intermediate A

2-bromo-cyclopenta[def]phenanthrene-4-one (1.0 g, 2.76 mmol) wasdissolved in dry ether (30 ml) and THF (10 ml), andphenylmagnesiumbromide (3.0M in ether) was gradually added thereto undera nitrogen gas atmosphere. The reaction mixture was refluxed for threehours, and water was added thereto so that the reaction was terminated.The resultant solution was adjusted to pH of 3-4 with a 1N—HCl solutionand extracted with ethyl ether. The organic phase was dried overanhydrous sodium sulfate, filtered, and concentrated under a reducedpressure. The resultant solid was purified by silica gel columnchromatography to give an intermediate A as a solid phase (0.79 g, 65%).

3) Synthesis of Compound 3

The intermediate A (0.79 g, 1.79 mmol) was dissolved in dry benzene (20ml), and trifluoromethanesulfonic acid (0.48 ml, 5.38 mmol, 3 eq.) wasdropwise added thereto. The reaction mixture was incubated at 80° C. fortwo hours. The resultant solution was diluted with water and extractedwith ethyl acetate. The organic phase was dried over anhydrous sodiumsulfate, filtered, and concentrated under a reduced pressure. Theresultant solid was purified by silica gel column chromatography andrecrystallized from a EtOAc-Hex mixed solvent to give a compound 3 as asolid phase (0.65 g, 63%). ¹H NMR (300 MHz, CDCl3, δ): 7.22-7.26 (m,10H), 7.70 (s, 2H), 7.80 (s, 3H), 8.00 (s, 2H)

Synthesis Example 3 1) Synthesis of Intermediate B

2-bromo-cyclopenta[def]phenanthrene-4-one (0.95 g, 3.35 mmol) and phenol(30 ml) were put into a 250 ml 3-neck round bottom flask. The reactionmixture was heated and incubated for five hours while a HCl gas was runinto the mixture. After the reaction was terminated, the reactionsolution was concentrated under a reduced pressure to remove unreactedphenol. The residue was purified by silica gel column chromatography togive an intermediate B (0.95 g, 62.5%).

2) Synthesis of Compound 4

The intermediate B (0.95 g, 2.1 mmol) was put into a 100 ml round bottomflask, and DMF (5 ml) and acetonitrile (20 ml) were added thereto. K₂CO₃(1.52 g) and octyl bromide (2.11 g) were sequentially added, and thereaction mixture was heated and refluxed for 18 hours. After thereaction was terminated, the organic phase was separated and purified bysilica gel column chromatography to give a compound 4 (0.70 g, 49%). ¹HNMR (300 MHz, CDCl₃, δ): 7.78 (2H, d), 7.79 (2H, s), 7.67 (2H, d), 7.64(1H, d), 7.11 (4H, dd), 6.76 (4H, dd), 3.89 (4H, t), 1.74 (4H, q), 1.28(20H, m), 0.88 (6H, m).

Synthesis Example 4 1) Synthesis of Intermediate C

2-bromobiphenyl (0.68 g, 2.95 mmol) was dissolved in anhydrous THF (10ml), and the reaction mixture was cooled to −78° C. Then, t-BuLi (3.5ml) was gradually dropwise added. The reaction mixture was stirred forone hour, and a solution of 2-bromo-cyclopenta[def]phenanthrene-4-one (1g, 3.53 mmol) in anhydrous THF (5 ml) was dropwise added thereto for 30minutes. After the reaction was terminated, the reaction solution wasconcentrated under a reduced pressure and extracted with ethylacetateand brine to separate an organic phase. The organic phase wasconcentrated and the residue was purified by silica gel columnchromatography to give an intermediate C (1.2 g).

2) Synthesis of Compound 5

The intermediate C was dissolved in acetic acid (30 ml), and thereaction mixture was cooled to 0° C. Then, a concentrated HCl (1 ml) wasdropwise added, and the reaction mixture was incubated for two hours.After the reaction was terminated, the reaction solution was filteredand washed with acetic acid and methanol to give a white solid (1.05 g,91%). ¹H NMR (300 MHz, CDCl3, δ): 7.22-7.26 (m, 8H), 7.70 (s, 2H), 7.80(s, 2H), 8.00 (s, 2H)

Synthesis of Emitting Materials 1) Synthesis of Material 1 (Formula 18)

The compound 2 (1.0 g, 1 eq., 2.02 mmol),4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane(0.77 g, 1 eq., 2.02 mmol), tetrakis(triphenylphosphine)palladium(0)(0.23 g, 0.1 eq., 0.2 mmol), 2M K₂CO₃ (1 ml, 1 eq., 2.02 mmol), andtetrabutylammoniumbromide (0.65 g, 1 eq., 2.02 mmol) were put into a 100ml round bottom flask under an argon gas atmosphere, and THF (50 ml) andtoluene (20 ml) were added thereto. The reaction mixture was refluxed at100° C. for 16 hours. When the reaction solution turned dark brown,water was added, and the resultant solution was extracted withethylacetate. The extracted organic phase was dried over anhydrousmagnesium sulfate and filtered to remove a solvent. The residue wasdissolved in a trace amount of toluene and purified on a silica gelcolumn. The resultant solid was recrystallized from toluene and methanolto give a material 1 represented by Formula 18 (0.71 g, 52%). ¹H NMR(300 MHz, CDCl₃, δ): 8.11 (s, 2H), 7.98 (s, 3H), 7.81 (s, 2H), 7.75-7.10(m, 13H), 1.93 (m, 4H), 1.21 (m, 20H), 0.87 (m, 6H), 0.65 (broad s, 4H).

2) Synthesis of Material 2 (Formula 19)

A material 2 represented by Formula 19 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2, and2-anthracene-9-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane was usedinstead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.15 (s, 2H), 7.95 (s, 3H), 7.78 (s, 2H),7.75-7.16 (m, 19H),

3) Synthesis of Material 3 (Formula 20)

A material 3 represented by Formula 20 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2. ¹H NMR (300 MHz, CDCl₃, δ): 8.13 (s,2H), 7.92 (s, 3H), 7.80 (s, 2H), 7.73-7.08 (m, 23H)

4) Synthesis of Material 4 (Formula 21)

A material 4 represented by Formula 21 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2, and4,4,5,5-tetramethyl-2-(10-naphthalene-2-yl-anthracene-9-yl)-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.11 (s, 2H), 7.96 (s, 3H), 7.81 (s, 2H),7.79-7.10 (m, 25H)

5) Synthesis of Material 5 (Formula 23)

A material 5 represented by Formula 23 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2, and4,4,5,5-tetramethyl-2-[10-(4-naphthalene-1-yl-phenyl)-anthracene-9-yl]-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.17 (s, 2H), 7.90 (s, 3H), 7.78 (s, 2H),7.75-7.01 (m, 29H)

6) Synthesis of Material 6 (Formula 26)

A material 6 represented by Formula 26 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2, and4,4,5,5-tetramethyl-2-(10-[1,1′,3′,1″]tetraphenyl-5′-yl-anthracene-9-yl)-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.02 (s, 2H), 7.98 (s, 3H), 7.92 (s, 2H),7.87-6.95 (m, 31H)

7) Synthesis of Material 7 (Formula 33)

A material 7 represented by Formula 33 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2, and4,4,5,5-tetramethyl-2-(3-methyl-10-naphthalene-1-yl-anthracene-9-yl)-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.09 (s, 2H), 7.88 (s, 3H), 7.83 (s, 2H),7.69-7.12 (m, 24H), 2.46 (s, 3H)

8) Synthesis of Material 8 (Formula 38)

A material 8 represented by Formula 38 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2, and4,4,5,5-tetramethyl-2-[10-(3-naphthalene-2-yl-phenyl)-anthracene-9-yl]-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.18 (s, 2H), 7.96 (s, 3H), 7.85 (s, 2H),7.74-7.02 (m, 29H)

9) Synthesis of Material 9 (Formula 40)

A material 9 represented by Formula 40 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 4was used instead of the compound 2. ¹H NMR (300 MHz, CDCl₃, δ): 8.11 (s,2H), 7.98 (s, 3H), 7.84 (s, 2H), 7.73-7.08 (m, 21H), 3.89 (4H, t), 1.74(4H, q), 1.28 (20H, m), 0.88 (6H, m)

10) Synthesis of Material 10 (Formula 42)

A material 10 represented by Formula 42 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2, anddi-naphthalene-2-yl-{4-[10-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl)-anthracene-9-yl]-phenyl}-aminewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.05 (s, 2H), 7.96 (s, 3H), 7.84 (s, 2H),7.69-6.81 (m, 36H)

11) Synthesis of Material 11 (Formula 46)

A material 11 represented by Formula 46 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 5was used instead of the compound 2. ¹H NMR (300 MHz, CDCl₃, δ): 8.13 (s,2H), 7.92 (s, 3H), 7.80 (s, 2H), 7.73-7.08 (m, 21H)

12) Synthesis of Material 12 (Formula 52)

A material 12 represented by Formula 52 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 5was used instead of the compound 2, and4,4,5,5-tetramethyl-2-(10-naphthalene-2-yl-anthracene-9-yl)-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.15 (s, 2H), 7.98 (s, 3H), 7.79 (s, 2H),7.75-7.18 (m, 23H)

13) Synthesis of Material 13 (Formula 53)

A material 13 represented by Formula 53 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 5was used instead of the compound 2, and2-(3-tert-butyl-10-naphthalene-1-yl-anthracene-9-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.13 (s, 2H), 7.92 (s, 3H), 7.80 (s, 2H),7.73-7.17 (m, 22H), 1.45 (s, 9H)

14) Synthesis of Material 14 (Formula 56)

A material 14 represented by Formula 56 was synthesized in the samemanner as in the synthesis of the material 1 except that compound 5 wasused instead of the compound 2, and2-{4-[9-naphthalene-2-yl-10-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolane-2-yl)-anthracene-2-yl]-phenyl}-1-phenyl-1H-benzoimidazolewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.13 (s, 2H), 8.05 (s, 3H), 7.95 (s, 2H),7.91-7.28 (m, 35H)

15) Synthesis of Material 15 (Formula 61)

A material 15 represented by Formula 61 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 3was used instead of the compound 2, and4,4,5,5-tetramethyl-2-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.11 (s, 2H), 7.88 (s, 3H), 7.83 (s, 2H),7.79-7.01 (m, 29H)

16) Synthesis of Material 16 (Formula 67)

A material 16 represented by Formula 67 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 5was used instead of the compound 2, and4,4,5,5-tetramethyl-2-[4-(10-naphthalene-2-yl-anthracene-9-yl)-phenyl]-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.11 (s, 2H), 7.89 (s, 3H), 7.81 (s, 2H),7.73-7.08 (m, 27H)

17) Synthesis of Material 17 (Formula 69)

A material 17 represented by Formula 69 was synthesized in the samemanner as in the synthesis of the material 1 except that the compound 5was used instead of the compound 2, and4,4,5,5-tetramethyl-2-[4-(3-methyl-10-naphthalene-1-yl-anthracene-9-yl)-naphthalene-1-yl]-[1,3,2]dioxaborolanewas used instead of4,4,5,5-tetramethyl-2-(10-phenyl-anthracene-9-yl)-[1,3,2]dioxaborolane.¹H NMR (300 MHz, CDCl₃, δ): 8.13 (s, 2H), 7.92 (s, 3H), 7.80 (s, 2H),7.73-7.08 (m, 20H), 2.44 (s, 3H)

As shown above, in the embodiments of the present invention, a lowmolecular weight compound obtained by reacting a cyclopentaphenanthrenecompound wherein the 2- or 6-position is functionalized with halogen,borate, aldehyde, hydroxyl, or the like, with another compound, is usedas an organoelectroluminescent material. Various substituents can beincorporated into the 4-position of the cyclopentaphenanthrene of thelow molecular weight compound, thereby enabling more stable filmformation and improving solubility in a solvent.

Evaluation Example Evaluation of Optical Characteristics of Materials

The photoluminescence (PL) spectra of the materials 1-9, 11-12, and 16in a solution phase and a film phase were measured to evaluate theemission characteristics of the materials 1-9, 11-12, and 16.

In order to evaluate optical characteristics of a solution phase, eachof the materials 1-9, 11-12, and 16 was diluted with toluene to aconcentration of 10 mM, and the PL spectra of the diluted solutions weremeasured using an ISC PC1 spectrofluorometer equipped with a xenon lamp.Also, in order to evaluate optical characteristics of a film phase,quartz substrates were prepared and washed with acetone and pure water.Then, the materials 1-9, 11-12, and 16 were spin-coated on thesubstrates and heated at 110° C. for 30 minutes to form films with athickness of 1,000 Å. The PL spectra of the films were measured. Theresults are presented in Table 1 below. As shown in Table 1, it can beseen that the materials 1-9, 11-12, and 16 according to the embodimentsof the present invention had emission characteristics suitable fororganoelectroluminescent devices.

TABLE 1 PL Material Solution (λ_(max))(nm) Film (λ_(max))(nm) 1 423, 440436 2 418, 436 434 3 423, 444 438 4 423, 443 435 5 424, 444 434 6 423,445 434 7 420, 440 430 8 434, 445 433 9 422, 443 440 11 425, 445 442 12426, 447 440 16 427, 448 443

Example 1

Organoelectroluminescent devices having the following structure weremanufactured using the material 1 as a host of an emitting layer and acompound of Formula 73 above as a dopant of the emitting layer:ITO/PEDOT(400 Å)/material 1: Formula 73 (300 Å)/Alq3 (40 Å)/LiF(10Å)/Al(2000 Å).

A 15 Ω/cm² (1,000 Å) ITO glass substrate was cut into pieces of 50 mm×50mm×0.7 mm in size, followed by ultrasonic cleaning in acetone, isopropylalcohol, and pure water (15 minutes for each) and then UV/ozone cleaning(30 minutes) to form anodes. PEDOT-PSS (Al4083) (Bayer) was coated onthe anodes and heated at 110° C. for five minutes in the atmosphere andthen at 200° C. for five minutes under a nitrogen atmosphere to formhole injection layers with a thickness of 400 Å. A mixture of 0.1 g ofthe host material 1 and 0.01 g of the compound of Formula 73 (10 partsby weight of the compound of Formula 73 based on 100 parts by weight ofthe material 1) were spin-coated on the hole injection layers and heatedat 100° C. for 30 minutes to form emitting layers with a thickness of300 Å. Then, an Alq3 compound was vacuum deposited to a thickness of 40Å on the emitting layers to form electron transport layers. LiF (10 Å,electron injection layers) and Al (2000 Å, cathodes) were sequentiallyvacuum-deposited on the electron transport layers to thereby completeorganoelectroluminescent devices as illustrated in FIG. 1A. Theorganoelectroluminescent devices exhibited blue emission of 7,300 cd/m²at a voltage of 8 V and efficiency of 2.8 cd/A.

Example 2

Organoelectroluminescent devices having the following structure weremanufactured using the material 2 as a host of an emitting layer and thecompound of Formula 73 above as a dopant of the emitting layer:ITO/Formula 74 (200 Å)/α-NPD(300 Å)/material 2: Formula 73 (300Å)/Alq3(40 Å)/LiF(10 Å)/Al(2000 Å).

A 15 Ω/cm² (1,000 Å) ITO glass substrate was cut into pieces of 50 mm×50mm×0.7 mm in size, followed by ultrasonic cleaning in acetone, isopropylalcohol, and pure water (15 minutes for each) and then UV/ozone cleaning(30 minutes) to form anodes. The compound of Formula 74 (hole injectionlayers) and α-NPD (hole transport layers) were vacuum deposited on theanodes, and a mixture of the material 2 and the compound of Formula 73(weight ratio of 100:10) was then vacuum deposited to form emittinglayers. Then, an Alq3 compound was vacuum deposited to a thickness of 40Å on the emitting layers to form electron transport layers. LiF (10 Å,electron injection layers) and Al (2000 Å, cathodes) were sequentiallyvacuum deposited on the electron transport layers to thereby completeorganoelectroluminescent devices as illustrated in FIG. 1B. Theorganoelectroluminescent devices exhibited blue emission of 12,000 cd/m²at a voltage of 7.5 V and efficiency of 6.32 cd/A.

Example 3

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material3 was used as a host of an emitting layer: ITO/Formula 74 (200Å)/α-NPD(300 Å)/material 3: Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 12,500 cd/m² at a voltage of 7.5V and efficiency of 9.4cd/A. The emission spectra of the organoelectroluminescent devices areillustrated in FIG. 2.

Example 4

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material4 was used as a host of an emitting layer: ITO/Formula 74 (200Å)/α-NPD(300 Å)/material 4 Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 15,400 cd/m² at a voltage of 7.5V and efficiency of 8.2cd/A.

Example 5

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material5 was used as a host of an emitting layer: ITO/Formula 74 (200Å)/α-NPD(300 Å)/material 5: Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 9,600 cd/m² at a voltage of 5.5 V and efficiency of 7.4cd/A.

Example 6

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material6 was used as a host of an emitting layer: ITO/Formula 74 (200Å)/α-NPD(300 Å)/material 6: Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 10,000 cd/m² at a voltage of 7.0 V and efficiency of 6.7cd/A.

Example 7

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material7 was used as a host of an emitting layer: ITO/Formula 74 (200Å)/α-NPD(300 Å)/material 7: Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 8,500 cd/m² at a voltage of 6.5 V and efficiency of 8.8cd/A.

Example 8

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material8 was used as a host of an emitting layer: ITO/Formula 74 (200Å)/α-NPD(300 Å)/material 8: Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 14,300 cd/m² at a voltage of 7.0 V and efficiency of 9.2cd/A.

Example 9

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 1 except that the material9 was used as a host of an emitting layer: ITO/PEDOT(400 Å)/material 9:Formula 73 (300 Å)/Alq3 (40 Å)/LiF(10 Å)/Al(2000 Å). Theorganoelectroluminescent devices exhibited blue emission of 9,400 cd/m²at a voltage of 8.0V and efficiency of 4.7 cd/A.

Example 10

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material11 was used as a host of an emitting layer: ITO/Formula 74 (200Å)/α-NPD(300 Å)/material 11: Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 12,200 cd/m² at a voltage of 7.5V and efficiency of 8.8cd/A.

Example 11

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material12 was used as a host of an emitting layer: ITO/Formula 71 (200Å)/α-NPD(300 Å)/material 12: Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 9,100 cd/m² at a voltage of 7.0V and efficiency of 6.8 cd/A.

Example 12

Organoelectroluminescent devices having the following structure weremanufactured in the same manner as in Example 2 except that the material16 was used as a host of an emitting layer: ITO/Formula 74 (200Å)/α-NPD(300 Å)/material 16: Formula 73 (300 Å)/Alq3(40 Å)/LiF(10Å)/Al(2000 Å). The organoelectroluminescent devices exhibited blueemission of 10,200 cd/m² at a voltage of 6.5 V and efficiency of 5.4cd/A.

The above Examples show that materials according to the embodiments ofthe present invention have good EL characteristics as phosphorescent andfluorescent materials.

A compound of Formula 1 according to the embodiment of the presentinvention is adapted for both dry and wet processes, and has goodemission characteristics and thermal stability. Therefore, the use ofthe compound of the present invention enables to produce anorganoelectroluminescent device having a low driving voltage and goodcolor purity and efficiency.

Other embodiments of the invention, including modifications andadaptions of the disclosed embodiments, will be apparent to thoseskilled in the art from consideration of the specification and practiceof the invention disclosed herein. The foregoing descriptions ofimplementations of the invention have been presented for purposes ofillustration and description. The descriptions are not exhaustive and donot limit the invention to the precise form disclosed. Modifications andvariations are possible in light of the above teachings or may beacquired from practicing the invention.

1. A cyclopentaphenanthrene-based compound represented by Formula 1:

wherein each Q is independently a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup; each Y is independently a substituted or unsubstituted C2-C30alkylene group, a substituted or unsubstituted C6-C30 cycloalkylenegroup, a substituted or unsubstituted C6-C30 arylene group, asubstituted or unsubstituted C2-C30 heteroarylene group, or asubstituted or unsubstituted C2-C30 alkenylene group; X is hydrogen,halogen, a cyano group, a hydroxyl group, a substituted or unsubstitutedC1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkylgroup, a substituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; m is an integer of 0 to 3, and when m is 2 or 3,Qs are the same or different from each other; n is an integer of 0 to 3,and when n is 2 or 3, Ys are the same or different from each other; R₁and R₂ are each independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group, and R₁ and R₂ can be optionally linked togetherto form a substituted or unsubstituted C3-C20 aliphatic ring, asubstituted or unsubstituted C5-C30 heteroaliphatic ring, a substitutedor unsubstituted C6-C30 aromatic ring, or a substituted or unsubstitutedC2-C30 heteroaromatic ring; R₃ through R₁₆ are each independentlyhydrogen, halogen, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 arylalkyl group, a substituted or unsubstituted C2-C30 heteroarylgroup, —N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ areeach independently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and R₁₉ is hydrogen, halogen, a cyano group, ahydroxyl group, or a substituted or unsubstituted C1-C20 alkyl group. 2.The cyclopentaphenanthrene-based compound of claim 1, wherein m is aninteger of 1 to 3, and n is an integer of 1 to
 3. 3. Thecyclopentaphenanthrene-based compound of claim 1, wherein the

in Formula 1 is represented by one of Formulae 2 through 5:

wherein each R₁₇ is independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C 2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and A is a single bond, O, S, Se, or (CH₂)_(p)where p is an integer of 1 to
 5. 4. The cyclopentaphenanthrene-basedcompound of claim 1, which is a compound selected from the groupconsisting of compounds represented by Formulae 6 through 8:

wherein each Q is independently a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup; each Y is independently a substituted or unsubstituted C2˜C30alkylene group, a substituted or unsubstituted C6˜C30 cycloalkylenegroup, a substituted or unsubstituted C6-C30 arylene group, asubstituted or unsubstituted C2-C30 heteroarylene group, or asubstituted or unsubstituted C2-C30 alkenylene group; X is hydrogen,halogen, a cyano group, a hydroxyl group, a substituted or unsubstitutedC1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkylgroup, a substituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; m is an integer of 0 to 3, and when m is 2 or 3,Qs are the same or different from each other; n is an integer of 0 to 3,and when n is 2 or 3, Ys are the same or different from each other; R₁′and R₂′ are each independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; R₉ through R₁₆ are each independently hydrogen,halogen, a cyano group, a hydroxyl group, a substituted or unsubstitutedC1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkylgroup, a substituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and each R₁₈ is independently hydrogen, halogen,a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group.
 5. The cyclopentaphenanthrene-based compound ofclaim 4, wherein in Formulae 6 through 8, -[Q]_(m)- is selected from thegroup consisting of chemical structures represented by Formulae 9Athrough 9R below:

wherein R′ and R″ are each independently hydrogen, halogen, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group.
 6. The cyclopentaphenanthrene-based compound ofclaim 4, wherein in Formulae 6 through 8, —[Y]_(n)—X is selected fromthe group consisting of chemical structures represented by Formulae 10Ato 10R, 11A to 11S, 12A to 12Q, 13A to 13LL, 14A to 14R, and 15A to 15Zbelow:

wherein R′ and R″ are each independently hydrogen, halogen, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group.
 7. The cyclopentaphenanthrene-based compound ofclaim 4, wherein m is an integer of 1 to 3, and n is an integer of 1 to3.
 8. The cyclopentaphenanthrene-based compound claim 1, which isselected from the group consisting of compounds represented by Formulae16 through 72 below:


9. An organoelectroluminescent device comprising: a first electrode; asecond electrode; and at least one organic layer interposed between thefirst electrode and the second electrode, the organic layer comprising acyclopentaphenanthrene-based compound represented by Formula 1:

wherein each Q is independently a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup; each Y is independently a substituted or unsubstituted C2-C30alkylene group, a substituted or unsubstituted C6-C30 cycloalkylenegroup, a substituted or unsubstituted C6-C30 arylene group, asubstituted or unsubstituted C2-C30 heteroarylene group, or asubstituted or unsubstituted C2-C30 alkenylene group; X is hydrogen,halogen, a cyano group, a hydroxyl group, a substituted or unsubstitutedC1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkylgroup, a substituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; m is an integer of 0 to 3, and when m is 2 or 3,Qs are the same or different from each other; n is an integer of 0 to 3,and when n is 2 or 3, Ys are the same or different from each other; R₁and R₂ are each independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group, and R₁ and R₂ can be optionally linked togetherto form a substituted or unsubstituted C3-C20 aliphatic ring, asubstituted or unsubstituted C5-C30 heteroaliphatic ring, a substitutedor unsubstituted C6-C30 aromatic ring, or a substituted or unsubstitutedC2-C30 heteroaromatic ring; R₃ through R₁₆ are each independentlyhydrogen, halogen, a cyano group, a hydroxyl group, a substituted orunsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20cycloalkyl group, a substituted or unsubstituted C5-C30 heterocycloalkylgroup, a substituted or unsubstituted C1-C20 alkoxy group, a substitutedor unsubstituted C6-C30 aryl group, a substituted or unsubstitutedC6-C30 arylalkyl group, a substituted or unsubstituted C2-C30 heteroarylgroup, —N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ areeach independently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and R₁₉ is hydrogen, halogen, a cyano group, ahydroxyl group, or a substituted or unsubstituted C1-C20 alkyl group.10. The organoelectroluminescent device of claim 9, wherein the organiclayer is an emitting layer, a hole injection layer, or a hole transportlayer.
 11. The organoelectroluminescent device of claim 9, wherein the

in Formula 1 is represented by one of Formulae 2 through 5:

wherein each R₁₇ is independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and A is a single bond, O, S, Se, or (CH₂)_(p)where p is an integer of 1 to
 5. 12. The organoelectroluminescent deviceof claim 9, wherein the cyclopentaphenanthrene-based compound isselected from the group consisting of compounds represented by Formulae6 through 8:

wherein each Q is independently a substituted or unsubstituted C6-C30arylene group or a substituted or unsubstituted C2-C30 heteroarylenegroup; each Y is independently a substituted or unsubstituted C2˜C30alkylene group, a substituted or unsubstituted C6˜C30 cycloalkylenegroup, a substituted or unsubstituted C6-C30 arylene group, asubstituted or unsubstituted C2-C30 heteroarylene group, or asubstituted or unsubstituted C2-C30 alkenylene group; X is hydrogen,halogen, a cyano group, a hydroxyl group, a substituted or unsubstitutedC1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkylgroup, a substituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; m is an integer of 0 to 3, and when m is 2 or 3,Qs are the same or different from each other; n is an integer of 0 to 3,and when n is 2 or 3, Ys are the same or different from each other; R₁′and R₂′ are each independently hydrogen, halogen, a cyano group, ahydroxyl group, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C3-C20 cycloalkyl group, a substituted orunsubstituted C5-C30 heterocycloalkyl group, a substituted orunsubstituted C1-C20 alkoxy group, a substituted or unsubstituted C6-C30aryl group, a substituted or unsubstituted C6-C30 aralkyl group, asubstituted or unsubstituted C2-C30 heteroaryl group, —N(Z₁)(Z₂) or—Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are each independentlyhydrogen, a substituted or unsubstituted C1-C20 alkyl group, asubstituted or unsubstituted C6-C30 aryl group, a substituted orunsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; R₉ through R₁₆ are each independently hydrogen,halogen, a cyano group, a hydroxyl group, a substituted or unsubstitutedC1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkylgroup, a substituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group; and each R₁₈ is independently hydrogen, halogen,a cyano group, a hydroxyl group, a substituted or unsubstituted C1-C20alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30aralkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group.
 13. The cyclopentaphenanthrene-based compound ofclaim 12, wherein in Formulae 6 through 8, -[Q]_(m)- is selected fromthe group consisting of chemical structures represented by Formulae 9Athrough 9R, and —[Y]_(n)—X is selected from the group consisting ofchemical structures represented by Formulae 10A to 10R, 11A to 11S, 12Ato 12Q, 13A to 13LL, 14A to 14R, and 15A to 15Z below:

wherein R′ and R″ are each independently hydrogen, halogen, a cyanogroup, a hydroxyl group, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C3-C20 cycloalkyl group, asubstituted or unsubstituted C5-C30 heterocycloalkyl group, asubstituted or unsubstituted C1-C20 alkoxy group, a substituted orunsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30arylalkyl group, a substituted or unsubstituted C2-C30 heteroaryl group,—N(Z₁)(Z₂) or —Si(Z₃)(Z₄)(Z₅) where Z₁, Z₂, Z₃, Z₄, and Z₅ are eachindependently hydrogen, a substituted or unsubstituted C1-C20 alkylgroup, a substituted or unsubstituted C6-C30 aryl group, a substitutedor unsubstituted C2-C30 heteroaryl group, a substituted or unsubstitutedC5-C20 cycloalkyl group, or a substituted or unsubstituted C5-C30heterocycloalkyl group.
 14. The organoelectroluminescent device of claim9, wherein the cyclopentaphenanthrene-based compound is selected fromthe group consisting of compounds represented by Formulae 16 through 72below:


15. The organoelectroluminescent device of claim 9, wherein said atleast one organic layer comprises an emitting layer comprised of thecyclopentaphenanthrene-based compound.
 16. The organoelectroluminescentdevice of claim 15, wherein the emitting layer further comprises afluorescent host material.
 17. The organoelectroluminescent device ofclaim 15, wherein the emitting layer further comprises a dopantmaterial.
 18. The organoelectroluminescent device of claim 15, whereinthe cyclopentaphenanthrene-based compound is used as a phosphorescenthost material.
 19. The organoelectroluminescent device of claim 18,wherein the emitting layer further comprises at least one of4,4′-N,N′-dicarbazole-biphenyl (CBP) and poly(n-vinylcarbazole) (PVK).20. The organoelectroluminescent device of claim 15, wherein theemitting layer comprises a host material represented by Formula 73 and adopant of the cyclopentaphenanthrene-based compound: